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Cheap flights from Jamaica to Illinois from $158

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Jamaica to Illinois departing on 5/20. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Jamaica to Illinois

Recent round-trip flight deals from Jamaica to Illinois

Enter your travel dates to find the best prices.
American Airlines Logo
1:15 pm - 5:55 pm
MBJ
-
ORD
4h 40mnonstop
American Airlines Logo
9:13 am - 1:23 pm
ORD
-
MBJ
4h 10mnonstop
$281American Airlines
Thu, May 7 - Tue, Jul 7
American Airlines Logo
1:15 pm - 5:55 pm
MBJ
-
ORD
4h 40mnonstop
American Airlines Logo
8:19 am - 4:14 pm
ORD
-
MBJ
7h 55m
1 stop
$286American Airlines
Thu, May 7 - Tue, Jul 7
United Airlines Logo
2:40 pm - 12:45 am
MBJ
-
ORD
10h 05m
1 stop
United Airlines Logo
6:30 am - 3:10 pm
ORD
-
MBJ
8h 40m
1 stop
$291United Airlines
Thu, May 7 - Tue, Jul 7
United Airlines Logo
4:12 pm - 2:20 pm
MBJ
-
ORD
22h 08m
1 stop
United Airlines Logo
9:56 pm - 1:30 pm
ORD
-
MBJ
15h 34m
1 stop
$292United Airlines
Fri, May 8 - Mon, May 11
American Airlines Logo
10:17 am - 5:58 pm
MBJ
-
ORD
7h 41m
1 stop
American Airlines Logo
8:46 pm - 9:13 am
ORD
-
MBJ
12h 27m
1 stop
$296American Airlines
Fri, May 8 - Fri, May 15
Frontier Logo
1:16 pm - 10:02 pm
MBJ
-
MDW
8h 46m
1 stop
Frontier Logo
6:00 am - 12:21 pm
MDW
-
MBJ
6h 21m
1 stop
$322Frontier
Thu, May 7 - Tue, Jul 7
Frontier Logo
1:16 pm - 10:02 pm
MBJ
-
MDW
8h 46m
1 stop
Frontier Logo
6:00 am - 12:11 pm
MDW
-
MBJ
6h 11m
1 stop
$334Frontier
Wed, May 20 - Tue, May 26
Multiple Airlines Logo
1:36 pm - 7:55 am
MBJ
-
ORD
18h 19m
2 stops
Multiple Airlines Logo
5:05 am - 12:31 pm
ORD
-
MBJ
7h 26m
1 stop
$376Multiple Airlines
Tue, May 19 - Tue, May 26
Southwest Logo
12:15 pm - 7:00 pm
MBJ
-
MDW
6h 45m
1 stop
Southwest Logo
10:05 am - 1:55 pm
MDW
-
MBJ
3h 50mnonstop
$422Southwest
Thu, May 7 - Tue, Jul 7
Southwest Logo
2:00 pm - 11:40 pm
MBJ
-
MDW
9h 40m
1 stop
Southwest Logo
7:50 am - 11:45 am
MDW
-
MBJ
3h 55mnonstop
$455Southwest
Sun, Jun 21 - Sun, Jul 19

Air Canada flights from Jamaica to Illinois

Our best Air Canada deals on Jamaica to Illinois flight tickets
Air Canada
Jun 10
MBJ12:30 pmMontego Bay Sangster Intl
21h 48m
2 stops
ORD10:18 amChicago O'Hare Intl
Jun 24
ORD8:40 pmChicago O'Hare Intl
14h 40m
1 stop
MBJ11:20 amMontego Bay Sangster Intl
$415
Air Canada
Jun 4
MBJ12:30 pmMontego Bay Sangster Intl
19h 15m
2 stops
ORD7:45 amChicago O'Hare Intl
Jun 8
ORD8:20 pmChicago O'Hare Intl
15h 00m
1 stop
MBJ11:20 amMontego Bay Sangster Intl
$421
Air Canada
Jun 4
MBJ12:30 pmMontego Bay Sangster Intl
19h 15m
2 stops
ORD7:45 amChicago O'Hare Intl
Jun 9
ORD1:55 pmChicago O'Hare Intl
21h 25m
2 stops
MBJ11:20 amMontego Bay Sangster Intl
$426

United Airlines flights from Jamaica to Illinois

Our best United Airlines deals on Jamaica to Illinois flight tickets
United Airlines
Apr 25
MBJ1:52 pmMontego Bay Sangster Intl
4h 23m
ORD6:15 pmChicago O'Hare Intl
May 1
ORD9:56 pmChicago O'Hare Intl
15h 34m
1 stop
MBJ1:30 pmMontego Bay Sangster Intl
$285
United Airlines
Apr 30
MBJ2:40 pmMontego Bay Sangster Intl
10h 46m
1 stop
ORD1:26 amChicago O'Hare Intl
May 6
ORD2:27 pmChicago O'Hare Intl
24h 43m
1 stop
MBJ3:10 pmMontego Bay Sangster Intl
$291
United Airlines
May 8
MBJ4:12 pmMontego Bay Sangster Intl
22h 08m
1 stop
ORD2:20 pmChicago O'Hare Intl
May 11
ORD9:56 pmChicago O'Hare Intl
15h 34m
1 stop
MBJ1:30 pmMontego Bay Sangster Intl
$292

momondo Fare Finder

 
Customize your flight search to find flights from Jamaica to Illinois that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated April 24, 2026.
Use the filters below to find and compare flights from Jamaica to Illinois that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 5/7

1:15 pm-5:55 pm

Nonstop4h 40m

Chicago O'Hare Intl

Tue 7/7

9:13 am-1:23 pm

Nonstop4h 10m

$281

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 5/7

1:15 pm-5:55 pm

Nonstop4h 40m

Chicago O'Hare Intl

Tue 7/7

8:19 am-4:14 pm

1 stop7h 55m

$286

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 5/7

2:40 pm-12:45 am

1 stop10h 05m

Chicago O'Hare Intl

Tue 7/7

6:30 am-3:10 pm

1 stop8h 40m

$291

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Fri 5/8

4:12 pm-2:20 pm

1 stop22h 08m

Chicago O'Hare Intl

Mon 5/11

9:56 pm-1:30 pm

1 stop15h 34m

$292

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Fri 5/8

10:17 am-5:58 pm

1 stop7h 41m

Chicago O'Hare Intl

Fri 5/15

8:46 pm-9:13 am

1 stop12h 27m

$296

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 5/7

1:16 pm-10:02 pm

1 stop8h 46m

Chicago Midway

Tue 7/7

6:00 am-12:21 pm

1 stop6h 21m

$322

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 5/20

1:16 pm-10:02 pm

1 stop8h 46m

Chicago Midway

Tue 5/26

6:00 am-12:11 pm

1 stop6h 11m

$334

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 5/19

1:36 pm-7:55 am

2 stops18h 19m

Chicago O'Hare Intl

Tue 5/26

5:05 am-12:31 pm

1 stop7h 26m

$376

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 5/7

12:15 pm-7:00 pm

1 stop6h 45m

Chicago Midway

Tue 7/7

10:05 am-1:55 pm

Nonstop3h 50m

$422

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sun 6/21

2:00 pm-11:40 pm

1 stop9h 40m

Chicago Midway

Sun 7/19

7:50 am-11:45 am

Nonstop3h 55m

$455

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Illinois from

How to get the cheapest flight ticket from Jamaica to Illinois

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Illinois?

The cheapest day to depart from Jamaica to Illinois is on a Wednesday when prices can be found for as low as $419. Flights from Jamaica to Illinois on a Monday will generally be more expensive and average around $543. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Illinois?

Our most recent data shows that the best time of day to fly to Illinois is in the afternoon. Flights from Jamaica to Illinois during this time can be as low as $454. Flights at noon are often more expensive with an average ticket price of $477.

What is the cheapest Jamaica to Illinois flight route?

Fly from Montego Bay Sangster Intl to Chicago O'Hare Intl for the best Jamaica - Illinois flight prices

What cabin class options are available on Jamaica to Illinois flights?

There are 3 cabin classes available to choose from on Jamaica to Illinois flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Jamaica to Illinois flights?

You could potentially save up to 5% on your flight if you consider stops on a Jamaica to Illinois flight.

Cheap Jamaica to Illinois flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Jamaica to Illinois

Best Price Found

$217

Fastest flight time

4h 05m

Direct flights

Every day

Airports in Illinois

98 airports
The best one-way flight to Illinois from Jamaica in the past 72 hours is $217. The best round-trip flight deal from Jamaica to Illinois found on momondo in the last 72 hours is $356.
The fastest flight from Jamaica to Illinois takes 4h 05m
Direct flights go from Jamaica to Illinois every day.
There are 98 airports in Illinois. From Jamaica there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).
Search flight deals

Frequently asked questions about flying from Jamaica to Illinois

  • When did momondo last update prices for flights from Jamaica to Illinois?

    Prices for flights from Jamaica to Illinois were last updated today.

  • How many operators does momondo search for flights from Jamaica to Illinois?

  • How old do you have to be to fly from Jamaica to Illinois?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Jamaica to Illinois.

  • What documentation or ID do you need to fly to Illinois?

    The travel and health documents you'll need for your trip to Illinois may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Illinois. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Jamaica to Illinois?

Best airlines flying from Jamaica to Illinois

Compare and see reviews for airlines that fly from Jamaica to Illinois with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $281Free CancellationRating
7.4
9,643 reviews
Search United Airlines flights
SouthwestPriceFrom $281Free CancellationRating
8.0
4,334 reviews
Search Southwest flights
American AirlinesPriceFrom $291Free CancellationRating
7.1
11,666 reviews
Search American Airlines flights
Spirit AirlinesPriceFrom $380Free CancellationRating
6.3
8,636 reviews
Search Spirit Airlines flights
DeltaPriceFrom $451Free CancellationRating
7.9
8,450 reviews
Search Delta flights

Why use momondo?

Why should I use momondo to find a flight deal from Jamaica to Illinois?

It is quick and easy to find Jamaica to Illinois flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Illinois that suits you.

Can I find flights from Jamaica to Illinois with flexible booking policies on momondo?

momondo does allow users to show only those flights to Illinois from Jamaica which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Jamaica to Illinois?

momondo provides multiple filters to help you find the best flight to Illinois from Jamaica. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Jamaica to Illinois right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Jamaica to Illinois now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Illinois and let you know when they change.

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